Strategies of Buying and Selling Simultaneously

Buying and Selling a Home at the Same Time

You may have found yourself in a position where you would like to buy one property while simultaneously selling another property. While doing this does present some unique challenges, it's completely possible to pull this off with the proper strategy and some degree of flexibility

The reasons and strategies for wanting to buy and sell simultaneously will differ from a primary homeowner looking to relocate to an investor seeking to execute a 1031 exchange to avoid capital gains taxes. In either instance, it's important to have a sound strategy and understand what the undertaking will involve. 

Selling A Primary Residence While Buying Another

There are several different ways to do this and how you do it will depend on your financial philosophies. There isn't necessarily a right and wrong way to approach this, some consider selling their home first the priority and then are willing to rent for a period of 6 months while they find the perfect replacement. This is usually the lowest stress avenue.

Some will be intent on executing the sale and purchase in such a way that both properties close in close succession to remove the extra step of renting. Money is a huge consideration for this move, particularly when financing is involved. In many instances, sellers will need the equity from the sale of their home to fund the down payment on the purchase of the second. 

If Financing is Necessary, Get Prequalified for a New Mortgage First

Before you get serious about selling your home, you should thoroughly research the possibility of buying a new primary residence. The Maui housing market can change rapidly at times, and the lending environment is changing as well. When you get prequalified with a local Maui lender, you can better determine your price range for a new home.

You can get accurate information about the interest rates available for your credit score and other qualifications. In addition, you can confirm that you can afford the loan payment for the size and quality of the home you are interested in.

Discuss Your Plans with a Real Estate Agent

After learning about your prequalification status, consulting with real estate agents in Maui is the next step. An experienced Maui real estate agent can help you determine how long your home may reasonably remain on the market.

In addition, you can get details on a realistic sales price. By analyzing the sales price in combination with closing costs and the current mortgage payoff balance, you can determine the sales proceeds that you have available for a down payment on your new home purchase. 

Newest Maui Properties For Sale

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Listing Image for 110 Kaanapali Shores Pl 518 1 of 35 Listing Image for 110 Kaanapali Shores Pl 518 2 of 35 Listing Image for 110 Kaanapali Shores Pl 518 3 of 35 Listing Image for 110 Kaanapali Shores Pl 518 4 of 35 Listing Image for 110 Kaanapali Shores Pl 518 5 of 35 Listing Image for 110 Kaanapali Shores Pl 518 6 of 35 Listing Image for 110 Kaanapali Shores Pl 518 7 of 35 Listing Image for 110 Kaanapali Shores Pl 518 8 of 35 Listing Image for 110 Kaanapali Shores Pl 518 9 of 35 Listing Image for 110 Kaanapali Shores Pl 518 10 of 35 Listing Image for 110 Kaanapali Shores Pl 518 11 of 35 Listing Image for 110 Kaanapali Shores Pl 518 12 of 35 Listing Image for 110 Kaanapali Shores Pl 518 13 of 35 Listing Image for 110 Kaanapali Shores Pl 518 14 of 35 Listing Image for 110 Kaanapali Shores Pl 518 15 of 35 Listing Image for 110 Kaanapali Shores Pl 518 16 of 35 Listing Image for 110 Kaanapali Shores Pl 518 17 of 35 Listing Image for 110 Kaanapali Shores Pl 518 18 of 35 Listing Image for 110 Kaanapali Shores Pl 518 19 of 35 Listing Image for 110 Kaanapali Shores Pl 518 20 of 35 Listing Image for 110 Kaanapali Shores Pl 518 21 of 35 Listing Image for 110 Kaanapali Shores Pl 518 22 of 35 Listing Image for 110 Kaanapali Shores Pl 518 23 of 35 Listing Image for 110 Kaanapali Shores Pl 518 24 of 35 Listing Image for 110 Kaanapali Shores Pl 518 25 of 35 Listing Image for 110 Kaanapali Shores Pl 518 26 of 35 Listing Image for 110 Kaanapali Shores Pl 518 27 of 35 Listing Image for 110 Kaanapali Shores Pl 518 28 of 35 Listing Image for 110 Kaanapali Shores Pl 518 29 of 35 Listing Image for 110 Kaanapali Shores Pl 518 30 of 35 Listing Image for 110 Kaanapali Shores Pl 518 31 of 35 Listing Image for 110 Kaanapali Shores Pl 518 32 of 35 Listing Image for 110 Kaanapali Shores Pl 518 33 of 35 Listing Image for 110 Kaanapali Shores Pl 518 34 of 35 Listing Image for 110 Kaanapali Shores Pl 518 35 of 35

$995,000

Mahana 518

110 Kaanapali Shores Pl 518, Kaanapali

1 Bed 1 Bath 820 SqFt Residential MLS® # 408764

Days on Market: 212

Living Maui Real Estate LLC Cell: 808-359-1161

In Escrow
Listing Image for 2345 Omaopio Rd 1 of 23 Listing Image for 2345 Omaopio Rd 2 of 23 Listing Image for 2345 Omaopio Rd 3 of 23 Listing Image for 2345 Omaopio Rd 4 of 23 Listing Image for 2345 Omaopio Rd 5 of 23 Listing Image for 2345 Omaopio Rd 6 of 23 Listing Image for 2345 Omaopio Rd 7 of 23 Listing Image for 2345 Omaopio Rd 8 of 23 Listing Image for 2345 Omaopio Rd 9 of 23 Listing Image for 2345 Omaopio Rd 10 of 23 Listing Image for 2345 Omaopio Rd 11 of 23 Listing Image for 2345 Omaopio Rd 12 of 23 Listing Image for 2345 Omaopio Rd 13 of 23 Listing Image for 2345 Omaopio Rd 14 of 23 Listing Image for 2345 Omaopio Rd 15 of 23 Listing Image for 2345 Omaopio Rd 16 of 23 Listing Image for 2345 Omaopio Rd 17 of 23 Listing Image for 2345 Omaopio Rd 18 of 23 Listing Image for 2345 Omaopio Rd 19 of 23 Listing Image for 2345 Omaopio Rd 20 of 23 Listing Image for 2345 Omaopio Rd 21 of 23 Listing Image for 2345 Omaopio Rd 22 of 23 Listing Image for 2345 Omaopio Rd 23 of 23

$1,995,000

↓ $355,000

Kula/Ulupalakua/Kanaio

2345 Omaopio Rd, Kula/Ulupalakua/Kanaio

2 Beds 2 Baths 1,014 SqFt Residential MLS® # 408762

Days on Market: 213

Live Maui Real Estate LLC

In Escrow
Listing Image for 339 Kai Malu Pl 58b 1 of 50 Listing Image for 339 Kai Malu Pl 58b 2 of 50 Listing Image for 339 Kai Malu Pl 58b 3 of 50 Listing Image for 339 Kai Malu Pl 58b 4 of 50 Listing Image for 339 Kai Malu Pl 58b 5 of 50 Listing Image for 339 Kai Malu Pl 58b 6 of 50 Listing Image for 339 Kai Malu Pl 58b 7 of 50 Listing Image for 339 Kai Malu Pl 58b 8 of 50 Listing Image for 339 Kai Malu Pl 58b 9 of 50 Listing Image for 339 Kai Malu Pl 58b 10 of 50 Listing Image for 339 Kai Malu Pl 58b 11 of 50 Listing Image for 339 Kai Malu Pl 58b 12 of 50 Listing Image for 339 Kai Malu Pl 58b 13 of 50 Listing Image for 339 Kai Malu Pl 58b 14 of 50 Listing Image for 339 Kai Malu Pl 58b 15 of 50 Listing Image for 339 Kai Malu Pl 58b 16 of 50 Listing Image for 339 Kai Malu Pl 58b 17 of 50 Listing Image for 339 Kai Malu Pl 58b 18 of 50 Listing Image for 339 Kai Malu Pl 58b 19 of 50 Listing Image for 339 Kai Malu Pl 58b 20 of 50 Listing Image for 339 Kai Malu Pl 58b 21 of 50 Listing Image for 339 Kai Malu Pl 58b 22 of 50 Listing Image for 339 Kai Malu Pl 58b 23 of 50 Listing Image for 339 Kai Malu Pl 58b 24 of 50 Listing Image for 339 Kai Malu Pl 58b 25 of 50 Listing Image for 339 Kai Malu Pl 58b 26 of 50 Listing Image for 339 Kai Malu Pl 58b 27 of 50 Listing Image for 339 Kai Malu Pl 58b 28 of 50 Listing Image for 339 Kai Malu Pl 58b 29 of 50 Listing Image for 339 Kai Malu Pl 58b 30 of 50 Listing Image for 339 Kai Malu Pl 58b 31 of 50 Listing Image for 339 Kai Malu Pl 58b 32 of 50 Listing Image for 339 Kai Malu Pl 58b 33 of 50 Listing Image for 339 Kai Malu Pl 58b 34 of 50 Listing Image for 339 Kai Malu Pl 58b 35 of 50 Listing Image for 339 Kai Malu Pl 58b 36 of 50 Listing Image for 339 Kai Malu Pl 58b 37 of 50 Listing Image for 339 Kai Malu Pl 58b 38 of 50 Listing Image for 339 Kai Malu Pl 58b 39 of 50 Listing Image for 339 Kai Malu Pl 58b 40 of 50 Listing Image for 339 Kai Malu Pl 58b 41 of 50 Listing Image for 339 Kai Malu Pl 58b 42 of 50 Listing Image for 339 Kai Malu Pl 58b 43 of 50 Listing Image for 339 Kai Malu Pl 58b 44 of 50 Listing Image for 339 Kai Malu Pl 58b 45 of 50 Listing Image for 339 Kai Malu Pl 58b 46 of 50 Listing Image for 339 Kai Malu Pl 58b 47 of 50 Listing Image for 339 Kai Malu Pl 58b 48 of 50 Listing Image for 339 Kai Malu Pl 58b 49 of 50 Listing Image for 339 Kai Malu Pl 58b 50 of 50

$2,195,000

↓ $195,000

Kai Malu 58B

339 Kai Malu Pl 58b, Wailea/Makena

3 Beds 2.5 Baths 1,796 SqFt Residential MLS® # 408760

Days on Market: 213

Keller Williams Realty Maui-Ka Cell: 808-385-0882

Listing Image for Pl 1 of 23 Listing Image for Pl 2 of 23 Listing Image for Pl 3 of 23 Listing Image for Pl 4 of 23 Listing Image for Pl 5 of 23 Listing Image for Pl 6 of 23 Listing Image for Pl 7 of 23 Listing Image for Pl 8 of 23 Listing Image for Pl 9 of 23 Listing Image for Pl 10 of 23 Listing Image for Pl 11 of 23 Listing Image for Pl 12 of 23 Listing Image for Pl 13 of 23 Listing Image for Pl 14 of 23 Listing Image for Pl 15 of 23 Listing Image for Pl 16 of 23 Listing Image for Pl 17 of 23 Listing Image for Pl 18 of 23 Listing Image for Pl 19 of 23 Listing Image for Pl 20 of 23 Listing Image for Pl 21 of 23 Listing Image for Pl 22 of 23 Listing Image for Pl 23 of 23

$4,150,000

Papohaku Ranchlands

Pl, Molokai

4 Beds 3.5 Baths 5,257 SqFt Residential MLS® # 408755

Days on Market: 216

Molokai Real Estate

Listing Image for 3060 S Kihei Rd 1 of 50 Listing Image for 3060 S Kihei Rd 2 of 50 Listing Image for 3060 S Kihei Rd 3 of 50 Listing Image for 3060 S Kihei Rd 4 of 50 Listing Image for 3060 S Kihei Rd 5 of 50 Listing Image for 3060 S Kihei Rd 6 of 50 Listing Image for 3060 S Kihei Rd 7 of 50 Listing Image for 3060 S Kihei Rd 8 of 50 Listing Image for 3060 S Kihei Rd 9 of 50 Listing Image for 3060 S Kihei Rd 10 of 50 Listing Image for 3060 S Kihei Rd 11 of 50 Listing Image for 3060 S Kihei Rd 12 of 50 Listing Image for 3060 S Kihei Rd 13 of 50 Listing Image for 3060 S Kihei Rd 14 of 50 Listing Image for 3060 S Kihei Rd 15 of 50 Listing Image for 3060 S Kihei Rd 16 of 50 Listing Image for 3060 S Kihei Rd 17 of 50 Listing Image for 3060 S Kihei Rd 18 of 50 Listing Image for 3060 S Kihei Rd 19 of 50 Listing Image for 3060 S Kihei Rd 20 of 50 Listing Image for 3060 S Kihei Rd 21 of 50 Listing Image for 3060 S Kihei Rd 22 of 50 Listing Image for 3060 S Kihei Rd 23 of 50 Listing Image for 3060 S Kihei Rd 24 of 50 Listing Image for 3060 S Kihei Rd 25 of 50 Listing Image for 3060 S Kihei Rd 26 of 50 Listing Image for 3060 S Kihei Rd 27 of 50 Listing Image for 3060 S Kihei Rd 28 of 50 Listing Image for 3060 S Kihei Rd 29 of 50 Listing Image for 3060 S Kihei Rd 30 of 50 Listing Image for 3060 S Kihei Rd 31 of 50 Listing Image for 3060 S Kihei Rd 32 of 50 Listing Image for 3060 S Kihei Rd 33 of 50 Listing Image for 3060 S Kihei Rd 34 of 50 Listing Image for 3060 S Kihei Rd 35 of 50 Listing Image for 3060 S Kihei Rd 36 of 50 Listing Image for 3060 S Kihei Rd 37 of 50 Listing Image for 3060 S Kihei Rd 38 of 50 Listing Image for 3060 S Kihei Rd 39 of 50 Listing Image for 3060 S Kihei Rd 40 of 50 Listing Image for 3060 S Kihei Rd 41 of 50 Listing Image for 3060 S Kihei Rd 42 of 50 Listing Image for 3060 S Kihei Rd 43 of 50 Listing Image for 3060 S Kihei Rd 44 of 50 Listing Image for 3060 S Kihei Rd 45 of 50 Listing Image for 3060 S Kihei Rd 46 of 50 Listing Image for 3060 S Kihei Rd 47 of 50 Listing Image for 3060 S Kihei Rd 48 of 50 Listing Image for 3060 S Kihei Rd 49 of 50 Listing Image for 3060 S Kihei Rd 50 of 50

$24,500,000

↓ $1,500,000

Kihei

3060 S Kihei Rd, Kihei

4 Beds 5.5 Baths 5,435 SqFt Residential MLS® # 408751

Days on Market: 216

Coldwell Banker Island Prop(S) Cell: 808-463-8485

Listing Image for 1011 S Kihei Rd B 1 of 32 Listing Image for 1011 S Kihei Rd B 2 of 32 Listing Image for 1011 S Kihei Rd B 3 of 32 Listing Image for 1011 S Kihei Rd B 4 of 32 Listing Image for 1011 S Kihei Rd B 5 of 32 Listing Image for 1011 S Kihei Rd B 6 of 32 Listing Image for 1011 S Kihei Rd B 7 of 32 Listing Image for 1011 S Kihei Rd B 8 of 32 Listing Image for 1011 S Kihei Rd B 9 of 32 Listing Image for 1011 S Kihei Rd B 10 of 32 Listing Image for 1011 S Kihei Rd B 11 of 32 Listing Image for 1011 S Kihei Rd B 12 of 32 Listing Image for 1011 S Kihei Rd B 13 of 32 Listing Image for 1011 S Kihei Rd B 14 of 32 Listing Image for 1011 S Kihei Rd B 15 of 32 Listing Image for 1011 S Kihei Rd B 16 of 32 Listing Image for 1011 S Kihei Rd B 17 of 32 Listing Image for 1011 S Kihei Rd B 18 of 32 Listing Image for 1011 S Kihei Rd B 19 of 32 Listing Image for 1011 S Kihei Rd B 20 of 32 Listing Image for 1011 S Kihei Rd B 21 of 32 Listing Image for 1011 S Kihei Rd B 22 of 32 Listing Image for 1011 S Kihei Rd B 23 of 32 Listing Image for 1011 S Kihei Rd B 24 of 32 Listing Image for 1011 S Kihei Rd B 25 of 32 Listing Image for 1011 S Kihei Rd B 26 of 32 Listing Image for 1011 S Kihei Rd B 27 of 32 Listing Image for 1011 S Kihei Rd B 28 of 32 Listing Image for 1011 S Kihei Rd B 29 of 32 Listing Image for 1011 S Kihei Rd B 30 of 32 Listing Image for 1011 S Kihei Rd B 31 of 32 Listing Image for 1011 S Kihei Rd B 32 of 32

$1,599,000

↓ $50,000

Kihei

1011 S Kihei Rd B, Kihei

5 Beds 3.5 Baths 2,359 SqFt Residential MLS® # 408728

Days on Market: 216

Compass-W

Listing Image for 426 Wailau Pl 1 of 50 Listing Image for 426 Wailau Pl 2 of 50 Listing Image for 426 Wailau Pl 3 of 50 Listing Image for 426 Wailau Pl 4 of 50 Listing Image for 426 Wailau Pl 5 of 50 Listing Image for 426 Wailau Pl 6 of 50 Listing Image for 426 Wailau Pl 7 of 50 Listing Image for 426 Wailau Pl 8 of 50 Listing Image for 426 Wailau Pl 9 of 50 Listing Image for 426 Wailau Pl 10 of 50 Listing Image for 426 Wailau Pl 11 of 50 Listing Image for 426 Wailau Pl 12 of 50 Listing Image for 426 Wailau Pl 13 of 50 Listing Image for 426 Wailau Pl 14 of 50 Listing Image for 426 Wailau Pl 15 of 50 Listing Image for 426 Wailau Pl 16 of 50 Listing Image for 426 Wailau Pl 17 of 50 Listing Image for 426 Wailau Pl 18 of 50 Listing Image for 426 Wailau Pl 19 of 50 Listing Image for 426 Wailau Pl 20 of 50 Listing Image for 426 Wailau Pl 21 of 50 Listing Image for 426 Wailau Pl 22 of 50 Listing Image for 426 Wailau Pl 23 of 50 Listing Image for 426 Wailau Pl 24 of 50 Listing Image for 426 Wailau Pl 25 of 50 Listing Image for 426 Wailau Pl 26 of 50 Listing Image for 426 Wailau Pl 27 of 50 Listing Image for 426 Wailau Pl 28 of 50 Listing Image for 426 Wailau Pl 29 of 50 Listing Image for 426 Wailau Pl 30 of 50 Listing Image for 426 Wailau Pl 31 of 50 Listing Image for 426 Wailau Pl 32 of 50 Listing Image for 426 Wailau Pl 33 of 50 Listing Image for 426 Wailau Pl 34 of 50 Listing Image for 426 Wailau Pl 35 of 50 Listing Image for 426 Wailau Pl 36 of 50 Listing Image for 426 Wailau Pl 37 of 50 Listing Image for 426 Wailau Pl 38 of 50 Listing Image for 426 Wailau Pl 39 of 50 Listing Image for 426 Wailau Pl 40 of 50 Listing Image for 426 Wailau Pl 41 of 50 Listing Image for 426 Wailau Pl 42 of 50 Listing Image for 426 Wailau Pl 43 of 50 Listing Image for 426 Wailau Pl 44 of 50 Listing Image for 426 Wailau Pl 45 of 50 Listing Image for 426 Wailau Pl 46 of 50 Listing Image for 426 Wailau Pl 47 of 50 Listing Image for 426 Wailau Pl 48 of 50 Listing Image for 426 Wailau Pl 49 of 50 Listing Image for 426 Wailau Pl 50 of 50

$11,500,000

↓ $500,000

Mahanalua Nui

426 Wailau Pl, Lahaina

5 Beds 7 Baths 6,682 SqFt Residential MLS® # 408714

Days on Market: 217

Coldwell Banker Island Prop-KP Cell: 808-214-4799

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Apply for a Home Equity Loan

While you may ideally want to sell your current house before buying a new one, this may not be an absolute requirement for some sellers. You could tap into your home’s equity by applying for an equity line of credit. Before moving forward with this possibility, be aware that the payment on the new home equity line will affect your debt-to-income ratio.

Mortgage lenders review your debt-to-income ratio as part of their qualification process. Because of this, you should discuss this option in detail with your lender to ensure that it will not impair your ability to qualify for a new mortgage.

Recent Sales on Maui

Sold
Closed: 07/20/2026
Listing Image for 3445 Lower Honoapiilani Rd 204 1 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 2 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 3 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 4 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 5 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 6 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 7 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 8 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 9 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 10 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 11 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 12 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 13 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 14 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 15 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 16 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 17 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 18 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 19 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 20 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 21 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 22 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 23 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 24 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 25 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 26 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 27 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 28 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 29 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 30 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 31 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 32 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 33 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 34 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 35 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 36 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 37 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 38 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 39 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 40 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 41 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 42 of 43 Listing Image for 3445 Lower Honoapiilani Rd 204 43 of 43

$1,085,000

↓ $65,000

Kaanapali Shores 204

3445 Lower Honoapiilani Rd 204, Kaanapali

2 Beds 2 Baths 988 SqFt Residential MLS® # 407640 Date Sold: July 20, 2026
Sold
Closed: 01/27/2026
Listing Image for 33 U'au Pl 1 of 50 Listing Image for 33 U'au Pl 2 of 50 Listing Image for 33 U'au Pl 3 of 50 Listing Image for 33 U'au Pl 4 of 50 Listing Image for 33 U'au Pl 5 of 50 Listing Image for 33 U'au Pl 6 of 50 Listing Image for 33 U'au Pl 7 of 50 Listing Image for 33 U'au Pl 8 of 50 Listing Image for 33 U'au Pl 9 of 50 Listing Image for 33 U'au Pl 10 of 50 Listing Image for 33 U'au Pl 11 of 50 Listing Image for 33 U'au Pl 12 of 50 Listing Image for 33 U'au Pl 13 of 50 Listing Image for 33 U'au Pl 14 of 50 Listing Image for 33 U'au Pl 15 of 50 Listing Image for 33 U'au Pl 16 of 50 Listing Image for 33 U'au Pl 17 of 50 Listing Image for 33 U'au Pl 18 of 50 Listing Image for 33 U'au Pl 19 of 50 Listing Image for 33 U'au Pl 20 of 50 Listing Image for 33 U'au Pl 21 of 50 Listing Image for 33 U'au Pl 22 of 50 Listing Image for 33 U'au Pl 23 of 50 Listing Image for 33 U'au Pl 24 of 50 Listing Image for 33 U'au Pl 25 of 50 Listing Image for 33 U'au Pl 26 of 50 Listing Image for 33 U'au Pl 27 of 50 Listing Image for 33 U'au Pl 28 of 50 Listing Image for 33 U'au Pl 29 of 50 Listing Image for 33 U'au Pl 30 of 50 Listing Image for 33 U'au Pl 31 of 50 Listing Image for 33 U'au Pl 32 of 50 Listing Image for 33 U'au Pl 33 of 50 Listing Image for 33 U'au Pl 34 of 50 Listing Image for 33 U'au Pl 35 of 50 Listing Image for 33 U'au Pl 36 of 50 Listing Image for 33 U'au Pl 37 of 50 Listing Image for 33 U'au Pl 38 of 50 Listing Image for 33 U'au Pl 39 of 50 Listing Image for 33 U'au Pl 40 of 50 Listing Image for 33 U'au Pl 41 of 50 Listing Image for 33 U'au Pl 42 of 50 Listing Image for 33 U'au Pl 43 of 50 Listing Image for 33 U'au Pl 44 of 50 Listing Image for 33 U'au Pl 45 of 50 Listing Image for 33 U'au Pl 46 of 50 Listing Image for 33 U'au Pl 47 of 50 Listing Image for 33 U'au Pl 48 of 50 Listing Image for 33 U'au Pl 49 of 50 Listing Image for 33 U'au Pl 50 of 50

$1,350,000

↓ $99,000

Kulamanu

33 U'au Pl, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 1,687 SqFt Residential MLS® # 407641 Date Sold: January 27, 2026
Sold
Closed: 11/05/2025
Listing Image for 174 Welau Way 1 of 38 Listing Image for 174 Welau Way 2 of 38 Listing Image for 174 Welau Way 3 of 38 Listing Image for 174 Welau Way 4 of 38 Listing Image for 174 Welau Way 5 of 38 Listing Image for 174 Welau Way 6 of 38 Listing Image for 174 Welau Way 7 of 38 Listing Image for 174 Welau Way 8 of 38 Listing Image for 174 Welau Way 9 of 38 Listing Image for 174 Welau Way 10 of 38 Listing Image for 174 Welau Way 11 of 38 Listing Image for 174 Welau Way 12 of 38 Listing Image for 174 Welau Way 13 of 38 Listing Image for 174 Welau Way 14 of 38 Listing Image for 174 Welau Way 15 of 38 Listing Image for 174 Welau Way 16 of 38 Listing Image for 174 Welau Way 17 of 38 Listing Image for 174 Welau Way 18 of 38 Listing Image for 174 Welau Way 19 of 38 Listing Image for 174 Welau Way 20 of 38 Listing Image for 174 Welau Way 21 of 38 Listing Image for 174 Welau Way 22 of 38 Listing Image for 174 Welau Way 23 of 38 Listing Image for 174 Welau Way 24 of 38 Listing Image for 174 Welau Way 25 of 38 Listing Image for 174 Welau Way 26 of 38 Listing Image for 174 Welau Way 27 of 38 Listing Image for 174 Welau Way 28 of 38 Listing Image for 174 Welau Way 29 of 38 Listing Image for 174 Welau Way 30 of 38 Listing Image for 174 Welau Way 31 of 38 Listing Image for 174 Welau Way 32 of 38 Listing Image for 174 Welau Way 33 of 38 Listing Image for 174 Welau Way 34 of 38 Listing Image for 174 Welau Way 35 of 38 Listing Image for 174 Welau Way 36 of 38 Listing Image for 174 Welau Way 37 of 38 Listing Image for 174 Welau Way 38 of 38

$3,000,000

Summit Estates

174 Welau Way, Kaanapali

4 Beds 4.5 Baths 2,771 SqFt Residential MLS® # 407639 Date Sold: November 5, 2025
Sold
Closed: 04/02/2026
Listing Image for 162 Aha'aina Way 1 of 32 Listing Image for 162 Aha'aina Way 2 of 32 Listing Image for 162 Aha'aina Way 3 of 32 Listing Image for 162 Aha'aina Way 4 of 32 Listing Image for 162 Aha'aina Way 5 of 32 Listing Image for 162 Aha'aina Way 6 of 32 Listing Image for 162 Aha'aina Way 7 of 32 Listing Image for 162 Aha'aina Way 8 of 32 Listing Image for 162 Aha'aina Way 9 of 32 Listing Image for 162 Aha'aina Way 10 of 32 Listing Image for 162 Aha'aina Way 11 of 32 Listing Image for 162 Aha'aina Way 12 of 32 Listing Image for 162 Aha'aina Way 13 of 32 Listing Image for 162 Aha'aina Way 14 of 32 Listing Image for 162 Aha'aina Way 15 of 32 Listing Image for 162 Aha'aina Way 16 of 32 Listing Image for 162 Aha'aina Way 17 of 32 Listing Image for 162 Aha'aina Way 18 of 32 Listing Image for 162 Aha'aina Way 19 of 32 Listing Image for 162 Aha'aina Way 20 of 32 Listing Image for 162 Aha'aina Way 21 of 32 Listing Image for 162 Aha'aina Way 22 of 32 Listing Image for 162 Aha'aina Way 23 of 32 Listing Image for 162 Aha'aina Way 24 of 32 Listing Image for 162 Aha'aina Way 25 of 32 Listing Image for 162 Aha'aina Way 26 of 32 Listing Image for 162 Aha'aina Way 27 of 32 Listing Image for 162 Aha'aina Way 28 of 32 Listing Image for 162 Aha'aina Way 29 of 32 Listing Image for 162 Aha'aina Way 30 of 32 Listing Image for 162 Aha'aina Way 31 of 32 Listing Image for 162 Aha'aina Way 32 of 32

$805,000

↓ $57,500

Leialoha

162 Aha'aina Way, Kihei

2 Beds 1 Bath 720 SqFt Residential MLS® # 407637 Date Sold: April 2, 2026
Buying Real Estate on Maui

Buying Real Estate on Maui

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Sold
Closed: 03/10/2026
Listing Image for 11 Keola Pl 1 of 45 Listing Image for 11 Keola Pl 2 of 45 Listing Image for 11 Keola Pl 3 of 45 Listing Image for 11 Keola Pl 4 of 45 Listing Image for 11 Keola Pl 5 of 45 Listing Image for 11 Keola Pl 6 of 45 Listing Image for 11 Keola Pl 7 of 45 Listing Image for 11 Keola Pl 8 of 45 Listing Image for 11 Keola Pl 9 of 45 Listing Image for 11 Keola Pl 10 of 45 Listing Image for 11 Keola Pl 11 of 45 Listing Image for 11 Keola Pl 12 of 45 Listing Image for 11 Keola Pl 13 of 45 Listing Image for 11 Keola Pl 14 of 45 Listing Image for 11 Keola Pl 15 of 45 Listing Image for 11 Keola Pl 16 of 45 Listing Image for 11 Keola Pl 17 of 45 Listing Image for 11 Keola Pl 18 of 45 Listing Image for 11 Keola Pl 19 of 45 Listing Image for 11 Keola Pl 20 of 45 Listing Image for 11 Keola Pl 21 of 45 Listing Image for 11 Keola Pl 22 of 45 Listing Image for 11 Keola Pl 23 of 45 Listing Image for 11 Keola Pl 24 of 45 Listing Image for 11 Keola Pl 25 of 45 Listing Image for 11 Keola Pl 26 of 45 Listing Image for 11 Keola Pl 27 of 45 Listing Image for 11 Keola Pl 28 of 45 Listing Image for 11 Keola Pl 29 of 45 Listing Image for 11 Keola Pl 30 of 45 Listing Image for 11 Keola Pl 31 of 45 Listing Image for 11 Keola Pl 32 of 45 Listing Image for 11 Keola Pl 33 of 45 Listing Image for 11 Keola Pl 34 of 45 Listing Image for 11 Keola Pl 35 of 45 Listing Image for 11 Keola Pl 36 of 45 Listing Image for 11 Keola Pl 37 of 45 Listing Image for 11 Keola Pl 38 of 45 Listing Image for 11 Keola Pl 39 of 45 Listing Image for 11 Keola Pl 40 of 45 Listing Image for 11 Keola Pl 41 of 45 Listing Image for 11 Keola Pl 42 of 45 Listing Image for 11 Keola Pl 43 of 45 Listing Image for 11 Keola Pl 44 of 45 Listing Image for 11 Keola Pl 45 of 45

$1,375,000

Makawao Ranch Acres

11 Keola Pl, Makawao/Olinda/Haliimaile

3 Beds 2 Baths 1,450 SqFt Residential MLS® # 407634 Date Sold: March 10, 2026
Sold
Closed: 02/19/2026
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$1,100,000

↓ $125,000

Maui Lani

33 Keoneloa St, Wailuku

3 Beds 2 Baths 2,114 SqFt Residential MLS® # 407624 Date Sold: February 19, 2026
View 6 More Listings

Consider a Bridge Loan

When looking at how to buy a house before selling yours, a bridge loan may be a great solution. A bridge loan, a short-term loan with a higher interest rate, can be used to refinance your current home mortgage or pull equity out as a second lien.

With interest-only payments, you can tap into your equity to use as a down payment to purchase a second home. You can also potentially decrease your first home’s mortgage payments, which will be beneficial if the closing dates do not align perfectly.

Choose a Low Down Payment Loan Program

While many mortgage lenders will require you to make a sizable down payment when you buy a house, there are lending solutions available that allow you to put down 5% or less. A Fannie Mae loan, for example, only requires 3% down. While the interest rates on these loans are competitive, you may be responsible for Mortgage Payment Insurance (MPI).

MPI could add hundreds of dollars to your monthly mortgage payment. With a low down payment loan, however, you may not need to access your current home’s equity to complete your purchase.

Borrow Against Your Retirement Account

Generally, your retirement account’s funds are inaccessible to you until you reach the age of 59.5 years old. Most withdrawals taken before you reach this age can trigger a penalty and will be taxable. However, the IRS allows you to withdraw funds without penalty to buy a house.

There are specific rules and requirements that you should research thoroughly before pursuing this option. Your retirement account funds can be used for a down payment as well as closing costs, and this could eliminate the need to sell your house before buying a new one.

Add a Contingency to the Sales Contract

If you have determined that the other options available are not suitable for your unique situation, another possibility is available. When considering how to buy a second home without selling the first, a sales contingency could be written into the new sales contract. A sales contingency can be worded so that your purchase is dependent on the sale of the current house. 

While this can seem like the perfect solution, be aware that many sellers may not accept this contingency. Like you, other sellers may be trying to sell their house to buy another property. If they delay their sale because of a sales contingency, they may not be able to structure their own timeline to suit their needs. Your real estate agent can work with you to structure a sales contingency with an agreeable seller.

Turn Your Home Into an Investment Property

If you are concerned about the possibility of having two mortgage payments at the same time, you could consider renting out your first home. The monthly rent from your rental property could cover its mortgage payment, property taxes, and other expenses. The remaining rental income is a profit that can be used as desired.

If you are unable to qualify for a new home loan for your purchase with the old mortgage in place, renting the property can help. Once you have a signed lease in place on your first home, your mortgage lender can apply that income to your debt-to-income ratio. 

Before turning your home into a rental, consult with your realtor. Your real estate agent can provide you with a fair market rental rate for the property. This information is required to determine if its monthly rent will cover its expenses. The IRS allows you to write off many property expenses, including upkeep costs, management fees, property taxes, etc. Depending on the situation, a property owner could possibly turn a profit on a rental house while enjoying a tax loss.

Consider Buying a Second Home

Buying a second home has advantages to consider as well. If you buy a second home, you can enjoy traveling back and forth between the locations as desired. When you are not using a home for personal use, you could rent it out as a rental property. A second home also has tax benefits

Even if you do not use the second home to produce rental income, you may qualify for the same homeowner tax deductions as you benefit from with your first home. Before buying a second home or turning your current home into a rental property, consider speaking to a tax advisor and a management company to explore all of the financial ramifications in detail.

Executing a 1031 Exchange

1031 Exchange Maui

When doing a 1031 exchange, you'll typically be selling the property you are going to exchange first and then immedietley seeking a replacement property. Read my full rundown on how to successfully navigate the process here

Explore Your Options Today

Keep in mind that you can combine multiple solutions presented here as you walk through the real estate process. For example, you could take out a home equity loan on your current home to access down payment funds to purchase your second home. At the same time, you could turn your first home into a rental property to generate monthly income.

This example is only one of many ways to combine these solutions and set up a scenario that suits your needs. Contact a local real estate agent to learn more about the housing and rental market.

Get In Touch With Evan!

Evan Harlow Maui

Evan Harlow ranks among the best real estate agents on Maui annually and is in the top 1% of Coldwell Banker agents worldwide in production. Evan has the expertise, experience, and work ethic to help you achieve your real estate buying and selling goals. We promise exceptional service and support from the beginning of the process through closing and beyond. See what Evan's clients are saying on Google.

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